Holiday rentals in Sheboygan County

4.83 out of 5 average rating, 267 reviews

Home Away From Home-One Block From Lake Michigan!

Centrally located and pet-friendly! Walk to the beach, parks, and downtown Sheboygan. This spacious two-story home perfect for groups features flexible bedroom setups, a fully equipped kitchen, dining room, fenced backyard, and parking for up to 4 vehicles. Base pricing is competitive for small groups $15/guest per night for more than 2 guests. Close to golf courses, many family spots, restaurants, and 16 miles from Road America. Watch “Sheboygan Airbnb” on YouTube for a full walkthrough!

5 out of 5 average rating, 126 reviews

Flat in Kohler

The Hemingway on Church - It Tolls For Thee

"Kristine's property has all the charm of a modern day Mayberry" -Michael This 1906 historic home is nestled in the heart of the equally historic "Village of Kohler." Completely remodeled in 2019 adding Kohler spa amenities and modern touches to its original charm. Mixing modern & antique furniture finds like the Hemingway Sideboard (which inspired the literary theme) make this historic hideaway a true Kohler destination. "You cannot get a better location in Kohler than this house!" -Dennis

4.9 out of 5 average rating, 135 reviews

Sheboygan Surf House - North Point

This super spacious studio apartment is the largest of our 3 spaces, located above Wisconsin's first Surf shop which is located in the heart of Sheboygan's Downtown District. Located directly next to bars , shopping and widely known restaurants like Tratoria Stephanos, Feild to Fork and IL Ritrovo, make walking everywhere easy. Whether you are here for beach days, a little get away or a wedding we are close to it all. Blue Harbor Resort, River front and the shores of Lake Michigan are close.

4.95 out of 5 average rating, 177 reviews

Home in Howards Grove

Spacious lower level priv entrance no cleaning fee

Not set up for babies or toddlers. Entire basement is for rent with a separate entrance. Kitchen area includes refrigerator, microwave, coffee pot, toaster, sink, dining table and chairs. NO STOVE OR OVEN IS AVAILABLE. Free Wifi and Cable TV. Air conditioning. Plenty of parking, keyless entry. 14 min to Road America, 13 min to Kohler, 9 min to Whistling Straits, 5 min to Lakeland University, 1 hr to Milwaukee, 1 hr to Green Bay. Lots of nice amenities, clean, spacious. No cleaning fee.

4.97 out of 5 average rating, 214 reviews

LUXE Manor With Modern, Elegant Vibes - 4,500 Sq

Modern chic blends with classic sophistication in this late 1800s Historic Manor, The Herman Hayssen House. Enjoy 4,500 sq ft of elegance and character that adorns this well-appointed home. Complete with 4 bedrooms, 3 full baths, and 1 half bath, many different areas for entertaining, both inside and out. The neighborhood is of the most elite in Sheboygan, situated between the lakefront and downtown and is a short drive to Whistling Straights and within an hour of Milwaukee and Green Bay.

4.98 out of 5 average rating, 202 reviews

Boutique Wellness Retreat - Hot Tub and Fireplace

Enjoy this beautifully landscaped and decorated boutique home. New patio and deck! Hot tub/Dry Sauna! Comfort and charm throughout. Cooks kitchen with all amenities. Primary bedroom with Stearns and Foster King size bed. The beautiful fireplace in the living room is perfect for a relaxing couples evening. Enjoy a glass of wine or local brew on the patio while you grill out. EV Charger and E-Bikes to explore the area. Sonos audio throughout. This beautiful boutique home is sure to impress!

4.71 out of 5 average rating, 109 reviews

Barn in Sheboygan Falls

Quiet Country Charm

Cozy barn loft with rustic charm. This newly renovated private loft sleeps 4 with the possibility of 1 or 2 more if you don’t mind sleeping on an air mattress. This room includes a bathroom with shower and small efficiency kitchen with microwave, coffee maker, and small refrigerator. The futon pulls out to a double bed. This relaxing local comes complete with barnyard animals for an authentic Wisconsin experience! You won’t forget the peaceful surroundings of this rustic destination.

5 out of 5 average rating, 147 reviews

Cabin in Cascade

hot tub and sauna on 5 private acres

Need a peaceful retreat? Experience 5 acres of tranquil, private woodland paradise. Cool nights are perfect for warming up in the hot tub or infrared sauna which overlook the meadow. Explore hiking trails and lakes that the scenic Kettle Moraine has to offer. Grill a delicious meal and later craft perfect s’mores by campfire as the crickets sing. Unwind at SoLu winery, just a minute down the road. Near Road America, Kettle Moraine State Forest, and Dundee. Your inspired getaway awaits!

5 out of 5 average rating, 215 reviews

Woodland Creek Retreat: explore & relax!

Lovely home nestled in 9 acres of peaceful woodland. 1.5 miles off I-43. Enjoy a walk in the woods or enjoy the dunes and wonderful views of Lake Michigan from Terry Andrae State Park only .2 miles away! Enjoy relaxing on the front porch or taking in the view of the woods from the spacious back deck. Be on the lookout for turkeys and deer. Wonderful wood burning fireplace and extensive game collection(500+) for staying in! We love the cozy and open cabin feel and hope you will too!

4.98 out of 5 average rating, 150 reviews

Lovely modern two bedroom home with fire pit

Newly renovated two bedroom home just a mile from the beach and five star restaurants. Enjoy a game of golf at world class Whistling Straight. Car enthusiasts will love Elkhart Lake Road America. Salmon fishing the Great Lake Michigan or just have a relaxing time around the fire pit. There is a laundry with washer/dryer, steamer and folding table. Dogs under 30 pounds. No cats sorry. No smoking in the house. Ample street parking at the front door. Fire pit in back yard.

4.96 out of 5 average rating, 191 reviews

Logan's Guest Nest

Logan's Guest Nest is located in a nice small town feel area. With a small look on the outside your Nest has a big feel on the inside. Spacious rooms and quiet area to rest after a day at the many beaches lining Lake Michigan. Or coming back from the races at Road America. Not to mention a day of golf at the many area courses, Whistling Straits maybe. All these wonderful outings are just minutes from the Nest. Plenty of local dinning or delivery for a nice ending of the day.

4.93 out of 5 average rating, 502 reviews

Cozy Sheboygan Upper

We began caring for this home and property in 2018, and this 1870's home needed some love. We have been steadily remodeling since we moved in and it's starting to feel pretty great. We're excited to share it and the neighborhood with you. We are two blocks west of North Beach/Deland Park, 4 blocks to the river front boardwalk, home to many restaurants, cafe's, and shops. We are also four quick blocks to downtown which hosts many more restaurants, shops, museums and parks.

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Popular amenities for Sheboygan County holiday rentals

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Other great holiday rentals in Sheboygan County

5 out of 5 average rating, 71 reviews

Recombobulation Station-Locally Owned Surf Escape

LynseyRating, 5 stars2 weeks ago

Missy and Kyle's apartment in Sheboygan was truly a great recombobulation station! The location was spectacular with only two blocks to Lake Michigan in one direction and two blocks to great dining, farmers market, coffee shops, and local shopping in the other direction. The apartment was incredibly clean, cozy, and comfortable for some rest and relaxation in-between our local adventures. It was a lovely home away from home with everything you would need to prepare meals. And in the event you've forgotten something at home, there is a good chance Missy has thought about it for you.

4.97 out of 5 average rating, 33 reviews

Apartment in Sheboygan

Heavenly Condo in the Malibu of the Midwest

MonicaRating, 5 stars2 days ago

This place was incredible! So close to the river walk and beach and in the perfect location for restaurants and only a 20 minute drive to Road America! Will definitely stay again!

5 out of 5 average rating, 16 reviews

Beachside Beautifully Renovated Historic Home

AmyRating, 5 stars19 months ago

Beautiful, well-appointed home with a heck of a view AND walking distance to downtown. Tricia was communicative and kind. Great experience!

4.93 out of 5 average rating, 45 reviews

Apartment in Sheboygan

Ellis District Urban Lake Condo

LorindaRating, 5 stars1 week ago

We absolutely loved our location so close to the beach and harbor area! We had everything needed for our stay. There is the perfect little ice cream shop a block away! Parking on the street available right in front of where we stayed. There is a book in the apartment with comments from previous guests with notes on great things they discovered while there as well. We contributed before our departure. We would absolutely consider another stay in the future if we visited again. Sheboygin is a beautiful place. Park across the street made it so easy to see out and over the harbor providing a great view allowing for a great walk to see things. Definitely a "10" in our books!

4.67 out of 5 average rating, 3 reviews

Villa in Sheboygan

Wandering Waves - Lakefront | Stay on the beach!

FaizahRating, 5 stars2 weeks ago

We loved our stay at this property right in front of the beach! Dan was great to communicate with and answered the few questions/concerns promptly and thoroughly. The condo was as described & pictured - clean, spacious, and well-stocked. We used the TV to browse different streaming services and enjoyed the easily accessible fireplace. The beds were quite comfortable and the two bathrooms were great to split up. Hopefully, we will return with more family in the near future!

4.97 out of 5 average rating, 95 reviews

Modern Lower Apt - One block to the Lake

JuneRating, 5 stars1 week ago

Michelle's place was one of the best Airbnbs we've stayed at! Her apartment was perfect for our family of 4. It was clean, comfortable, nicely decorated, and had extra touches, like water, snacks, and duck food. The location of her place was perfect. Walkable to Deland Park Beach, the red lighthouse, and Blast ice cream. It was 5 minutes away by car to South Pier which has shops and restaurants by the river. Sheboygan was a great place to relax for our family. I cannot recommend Michelle's place more!

4.95 out of 5 average rating, 59 reviews

Guest suite in Waldo

Above Garage Apartment w/ Private Beach

JennyRating, 5 stars3 days ago

Dustin’s place is a great space for couples. It is very clean and well equipped. He was very accommodating when I messaged him well after our arrival that we needed a place to charge our E-bikes. Dustin’s place was exactly what we needed and will rebook the next time we’re in the area. Highly recommend!